Dimethylformamide dimethyl acetal → (2E)-3-(dimethylamino)-1-[2-hydroxy-5-(trifluoromethyl)phenyl]prop-2-en-1-one

HRID 2283648Notes

Reaction equation

HRID 2283648 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[CH3:17][N:18]([CH3:20])/[CH:19]=[CH:13]/[C:12]([C:3]1[CH:4]=[C:5]([C:8]([F:9])([F:10])[F:11])[CH:6]=[CH:7][C:2]=1[OH:1])=[O:14]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 117695991-(2-Hydroxy-5-(trifluoromethyl)phenyl)ethan-1-one

Product 1

HCID 59436605(2E)-3-(dimethylamino)-1-[2-hydroxy-5-(trifluoromethyl)phenyl]prop-2-en-1-oneYield 73%

Conditions

Temperature
110 °C

Procedure

1-[2-Hydroxy-5-(trifluoromethyl)phenyl]ethanone, (Preparation 32, 7.0 g, 0.034 mol) was taken in dimethylformamide dimethylacetal (18.2 mL, 0.14 mol) at ambient temperature and then heated at 110° C. for 30 minutes. The reaction mixture was concentrated in vacuo and the crude product was crystallised from 2-propanol to afford the title compound as bright yellow solid (6.4 g, 73%). 1HNMR (CDCl3): δ 3.02 (s, 3H) 3.22 (s, 3H), 5.72 (d, 1H), 6.99 (d, 1H), 7.55 (d 1H), 7.89-7.94 (m, 2H), 14.45 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product was crystallised from 2-propanol

Sources & evidence

ORD record
ord-a38516ca135942f7b83b89e74caf9597
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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